CuI-catalyzed synthesis of 2-( tert -butyldisulfanyl) heterocycles from 2-mercaptoheterocycles and tert -butanesulfinamide

作者: Xingzhao Tu , Jing Xiong , Zhijie Li , Lihong Zhou , Christina Emmanouil

DOI: 10.1007/S00706-015-1618-1

关键词: tert-ButanesulfinamideCondensationChemistryCatalysisOrganic chemistry

摘要: The valuable 2-(tert-butyldisulfanyl)heterocycles were effectively synthesized from 2-mercaptoheterocycles and tert-butanesulfinamide via unusual condensation. reaction between 2-mercapto sulfur-containing heterocycles was performed under ligand-free CuI-catalyzed conditions. synthetic processes described herein are simple, cost-efficient, practical. Furthermore, a plausible mechanism is proposed for this transformation.

参考文章(29)
Arong Gaowa, Tomohisa Horibe, Masayuki Kohno, Yasuhiko Tabata, Hiroshi Harada, Masahiro Hiraoka, Koji Kawakami, Enhancement of anti-tumor activity of hybrid peptide in conjugation with carboxymethyl dextran via disulfide linkers. European Journal of Pharmaceutics and Biopharmaceutics. ,vol. 92, pp. 228- 236 ,(2015) , 10.1016/J.EJPB.2015.03.015
Xirui Lv, Qinjie Xiang, Qingle Zeng, Potassium Hydroxide-promoted SelectiveN-Monoalkylation of Chiralt-Butane- andp-Toluenesulfinamides Organic Preparations and Procedures International. ,vol. 46, pp. 164- 175 ,(2014) , 10.1080/00304948.2014.884373
Rainer E. Martin, Luke G. Green, Wolfgang Guba, Nicole Kratochwil, Andreas Christ, Discovery of the first nonpeptidic, small-molecule, highly selective somatostatin receptor subtype 5 antagonists: a chemogenomics approach. Journal of Medicinal Chemistry. ,vol. 50, pp. 6291- 6294 ,(2007) , 10.1021/JM701143P
Loris Grossi, Pier Carlo Montevecchi, Samantha Strazzari, S‐Nitrosothiol and Disulfide Formation through Peroxynitrite‐Promoted Oxidation of Thiols European Journal of Organic Chemistry. ,vol. 2001, pp. 131- 135 ,(2001) , 10.1002/1099-0690(200101)2001:1<131::AID-EJOC131>3.0.CO;2-N
Eun Kyoung Ryu, Yearn Seong Choe, Sang Sung Byun, Kyung-Han Lee, Dae Yoon Chi, Yong Choi, Byung-Tae Kim, None, Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake. Bioorganic & Medicinal Chemistry. ,vol. 12, pp. 859- 864 ,(2004) , 10.1016/J.BMC.2004.01.002
Simon J. Hocart, Rahul Jain, William A. Murphy, John E. Taylor, David H. Coy, Highly potent cyclic disulfide antagonists of somatostatin. Journal of Medicinal Chemistry. ,vol. 42, pp. 1863- 1871 ,(1999) , 10.1021/JM9806289
Lin Chen, Ivana Zoulíková, Jiřina Slaninová, George Barany, Synthesis and pharmacology of novel analogues of oxytocin and deaminooxytocin: Directed methods for the construction of disulfide and trisulfide bridges in peptides Journal of Medicinal Chemistry. ,vol. 40, pp. 864- 876 ,(1997) , 10.1021/JM9607156
Nazli B. McDonnell, Roberto N. De Guzman, William G. Rice, Jim A. Turpin, Michael F. Summers, Zinc ejection as a new rationale for the use of cystamine and related disulfide-containing antiviral agents in the treatment of AIDS Journal of Medicinal Chemistry. ,vol. 40, pp. 1969- 1976 ,(1997) , 10.1021/JM970147+